I've been dealing with wash sale reporting for years as a day trader, and what you're experiencing is actually pretty common. The key thing to understand is that both GainsKeeper and TradeLog are likely correct - they're just applying different but valid interpretations of the wash sale rules. The IRS allows flexibility in how you report wash sales on Form 8949 as long as you're consistent and don't ultimately avoid recognizing the disallowed losses. Some software applies adjustments immediately when the wash sale occurs, while others defer the adjustments until you exit the position completely. My advice would be to pick one method and stick with it consistently across all your trading. If you're unsure which to choose, the method that adjusts cost basis on replacement shares (like TradeLog did for your LINE 4) tends to be more widely accepted and is what most major brokerages use in their year-end tax documents. Just make sure your total gains/losses for the year are roughly the same between both systems - that's the real test of whether the calculations are equivalent.

I've dealt with this exact same frustration between different tax software platforms! One thing that helped me was creating a simple spreadsheet to manually verify a few key transactions where I saw the biggest discrepancies. Pick 2-3 of your most straightforward wash sale scenarios and calculate them by hand using the basic IRS rules: if you sell at a loss and buy substantially identical securities within 30 days before or after, the loss is disallowed and added to the cost basis of the replacement shares. This manual check helped me identify that one of my platforms was incorrectly grouping certain ETF trades as wash sales when they shouldn't have been (they tracked similar but not "substantially identical" funds). Once I understood where the core difference was coming from, I could make an informed decision about which platform's approach was more accurate for my specific situation. Also, don't forget to double-check that both platforms are using the same lot identification method (FIFO vs specific identification) - this can cause major differences in wash sale calculations even when the underlying logic is correct.

I'm so sorry for the loss of both your parents and the additional stress this dishonest tax preparer has caused during such a difficult time. This situation is unfortunately more common than it should be. Based on the excellent advice already shared here, I'd recommend a multi-pronged approach: 1. **Immediate action**: File Form 56 (Notice Concerning Fiduciary Relationship) with the IRS if you haven't already - this establishes your legal authority as executor for all tax matters. 2. **Document retrieval**: Submit Form 4506-T requesting both wage/income transcripts AND account transcripts. The account transcripts will show any estimated tax payments your parents made, which could significantly reduce what's owed. 3. **Direct contact**: Reach out to all income sources directly - state pension system, IRA custodians, banks, and any former employers. As executor, you have the right to request duplicate tax documents, and most institutions keep records for 7+ years. 4. **Professional help**: Consider an initial consultation with a CPA or Enrolled Agent experienced in deceased taxpayer returns. They can ensure you're requesting all necessary documents and help navigate the penalty abatement process. 5. **State board complaint**: Definitely file a complaint against this tax preparer with your state's board of accountancy. Her conduct is highly unethical and the investigation may pressure her to return documents or at least officially acknowledge she lost them. Document every step you take - this persistence and good faith effort will be crucial if you need to request penalty relief later. The IRS has reasonable cause provisions specifically for situations like yours where the delay was caused by circumstances beyond your control.

I'm so sorry for your losses and the additional frustration this unethical tax preparer has caused during an already overwhelming time. What she did - claiming to file taxes when she didn't and then refusing to return documents - is completely unacceptable. The advice here about Form 4506-T for transcripts is excellent, but I'd also suggest checking if your parents had any health savings accounts (HSAs) or received any unemployment compensation in 2020, as these are often overlooked income sources that would appear on the wage and income transcripts. Since you mentioned they were both retired and typically owed taxes, they likely had multiple income streams that required careful coordination. Consider requesting both the wage/income transcripts AND the account transcripts simultaneously - the account transcripts will show if they made any estimated quarterly payments that could significantly reduce the final tax liability. One additional resource that might help: if your parents used the same bank for many years, their banker might have copies of prior year tax returns in their loan files or safe deposit box records. It's worth asking, especially if they had mortgages or other loans where tax returns were required. Keep documenting every attempt you make to resolve this - your persistent good faith efforts will be crucial if you need penalty relief later. The IRS recognizes that executor situations often involve circumstances beyond your control, and your thorough approach demonstrates exactly the kind of reasonable diligence they look for when considering penalty abatement. You're doing everything right in a truly difficult situation.

Anyone know if hardware wallets like Ledger complicate this? I transfer from Coinbase to my Ledger for security, then sometimes back to an exchange if I want to sell.

Just to add some clarity from an accounting perspective - the key concept here is "constructive receipt." When you transfer crypto between exchanges or wallets you control, you haven't actually disposed of the asset or received anything new of value. You still own the same crypto, just stored in a different location. Think of it like moving cash from your checking account to your savings account - you're not creating a taxable event, just relocating your asset. The IRS Publication 544 covers this under "Sales and Other Dispositions of Assets" if you want the official guidance. One important note though: always verify the receiving address before transferring. Unlike traditional banking, crypto transfers can't be reversed if you send to the wrong address. That would actually be a loss you could potentially deduct! Keep detailed records of all transfers including transaction IDs, timestamps, and wallet addresses. While transfers aren't taxable, having complete documentation protects you if the IRS ever questions your reporting.

One thing that really helped me understand this better was learning about the "netting" process that happens on Schedule D. The IRS requires you to first net all your short-term gains and losses together, then net all your long-term gains and losses separately. Since all your trades were within the same year, they're all short-term. So your $800 in gains minus $300 in losses gives you a net short-term capital gain of $500 - that's what gets taxed at your ordinary income rate. The $3,000 deduction limit only kicks in when you have an overall net loss across all your capital transactions for the year. Think of it as: gains and losses offset each other first, then any remaining net loss (up to $3,000) can reduce your regular taxable income. Keep track of your cost basis for everything - you'll need the purchase date, sale date, purchase price, and sale price for each transaction when you file. Many brokers provide this in a consolidated 1099-B form, but it's good to keep your own records too.

Great discussion everyone! I wanted to add one more important point about timing that might help others. Since you mentioned all your trades were within the same year, they're classified as short-term capital gains/losses. But if you're planning ahead for next year, remember that holding investments for more than one year before selling qualifies them as long-term capital gains, which get preferential tax treatment. Long-term capital gains are taxed at 0%, 15%, or 20% depending on your income level, which is usually much better than the short-term rate (which is just your regular income tax rate). So if you have some winners you're thinking about selling, it might be worth waiting until you've held them over a year if you're not in immediate need of the cash. Also, when doing tax-loss harvesting near year-end, consider the settlement dates, not just the trade dates. Stock trades typically settle T+2 (two business days after the trade), so if you want losses to count for this tax year, you generally need to execute the sale by the last few business days of December to ensure settlement occurs before January 1st.

I went through this exact situation two years ago and completely understand the stress! Here's what worked for me: First, don't panic about the accuracy of your Form 4852 estimates. The IRS knows you're working with limited information and they're reasonable about good faith estimates. Use your bank statements to calculate gross income, and for withholding estimates, you can use online calculators based on your filing status and number of allowances. One thing that really helped me was checking if my employers filed electronically with the IRS. Even though I couldn't get my physical W-2s, the information was already in the IRS system. You can request a wage and income transcript from the IRS website (irs.gov) which shows exactly what employers reported for you. This gives you the precise numbers for Form 4852 instead of guessing. For California extensions, yes you need to file separately - Form FTB 3519. The federal extension doesn't automatically cover state filing. Also, if you do file an extension, remember it's just for filing the return, not for paying any taxes owed. If you think you'll owe money, try to estimate and pay that by April 15th to avoid penalties. You've got this! The IRS deals with missing W-2 situations all the time and Form 4852 exists exactly for cases like yours.

I'm dealing with a very similar situation right now! Lost my W-2s during a move and feeling totally overwhelmed. Thank you so much to everyone who's shared their experiences - this thread is a goldmine of practical advice. I'm particularly interested in the wage and income transcript option that Kai mentioned. It sounds like that could give me the exact numbers I need instead of trying to estimate from bank statements. Has anyone here actually used the online transcript service recently? I'm wondering how current the information is - like if my employers filed their reports in January, would that data already be available in the IRS system? Also seeing some great suggestions about different tax software options. I was planning to use TurboTax but it sounds like H&R Block and FreeTaxUSA both handle Form 4852 well. Has anyone compared how user-friendly these different platforms are for this specific situation? Really appreciate this community - you're all helping reduce my stress level significantly!